IL187409A - Sulfonamide derivatives useful as liver carnitine palmitoyl transferase (l-cpt1) inhibitors - Google Patents

Sulfonamide derivatives useful as liver carnitine palmitoyl transferase (l-cpt1) inhibitors

Info

Publication number: IL187409A
Authority: IL; Israel
Prior art keywords: benzenesulfonylamino; alkyl; benzoylamino; benzoic acid; chloro
Prior art date: 2005-06-06

Application number

IL187409A

Other languages

English (en)

Other versions

IL187409A0 (en

Original Assignee

Hoffmann La Roche

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2005-06-06

Filing date

2007-11-15

Publication date

2012-03-29

2007-11-15 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

2008-02-09 Publication of IL187409A0 publication Critical patent/IL187409A0/en

2012-03-29 Publication of IL187409A publication Critical patent/IL187409A/en

Links

239000003112 inhibitor Substances 0.000 title claims description 11
229940124530 sulfonamide Drugs 0.000 title abstract description 6
150000003456 sulfonamides Chemical class 0.000 title abstract description 5
210000004185 liver Anatomy 0.000 title description 11
108010018424 Carnitine O-palmitoyltransferase Proteins 0.000 title description 5
102000002666 Carnitine O-palmitoyltransferase Human genes 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims abstract description 141
150000002148 esters Chemical class 0.000 claims abstract description 24
150000003839 salts Chemical class 0.000 claims abstract description 22
101000859570 Homo sapiens Carnitine O-palmitoyltransferase 1, liver isoform Proteins 0.000 claims abstract description 6
239000003814 drug Substances 0.000 claims abstract description 6
102100027943 Carnitine O-palmitoyltransferase 1, liver isoform Human genes 0.000 claims abstract 3
229910052739 hydrogen Inorganic materials 0.000 claims description 52
229910052736 halogen Inorganic materials 0.000 claims description 49
150000002367 halogens Chemical group 0.000 claims description 49
239000001257 hydrogen Substances 0.000 claims description 49
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 48
239000005711 Benzoic acid Substances 0.000 claims description 47
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 33
229910052799 carbon Inorganic materials 0.000 claims description 25
-1 3,5-dichloro-phenyl Chemical group 0.000 claims description 24
229910052757 nitrogen Inorganic materials 0.000 claims description 23
125000001072 heteroaryl group Chemical group 0.000 claims description 22
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 21
238000000034 method Methods 0.000 claims description 21
125000004093 cyano group Chemical group *C#N 0.000 claims description 17
125000001424 substituent group Chemical group 0.000 claims description 15
201000010099 disease Diseases 0.000 claims description 14
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical group [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 13
238000011321 prophylaxis Methods 0.000 claims description 12
125000003118 aryl group Chemical group 0.000 claims description 11
230000001225 therapeutic effect Effects 0.000 claims description 10
201000001421 hyperglycemia Diseases 0.000 claims description 9
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 8
206010012601 diabetes mellitus Diseases 0.000 claims description 8
239000008103 glucose Substances 0.000 claims description 8
238000011282 treatment Methods 0.000 claims description 8
208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 8
201000001320 Atherosclerosis Diseases 0.000 claims description 7
206010007559 Cardiac failure congestive Diseases 0.000 claims description 7
206010019280 Heart failures Diseases 0.000 claims description 7
208000035150 Hypercholesterolemia Diseases 0.000 claims description 7
208000031226 Hyperlipidaemia Diseases 0.000 claims description 7
206010020772 Hypertension Diseases 0.000 claims description 7
208000031773 Insulin resistance syndrome Diseases 0.000 claims description 7
208000001145 Metabolic Syndrome Diseases 0.000 claims description 7
208000008589 Obesity Diseases 0.000 claims description 7
208000001647 Renal Insufficiency Diseases 0.000 claims description 7
201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 7
239000013543 active substance Substances 0.000 claims description 7
208000035475 disorder Diseases 0.000 claims description 7
208000010706 fatty liver disease Diseases 0.000 claims description 7
201000006370 kidney failure Diseases 0.000 claims description 7
235000020824 obesity Nutrition 0.000 claims description 7
230000007170 pathology Effects 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
BJACXOCJPLSUML-UHFFFAOYSA-N 4-[[3-[(5-chloro-2-methoxyphenyl)sulfonylamino]-4,5-dimethoxybenzoyl]amino]benzoic acid Chemical compound COC1=CC=C(Cl)C=C1S(=O)(=O)NC1=CC(C(=O)NC=2C=CC(=CC=2)C(O)=O)=CC(OC)=C1OC BJACXOCJPLSUML-UHFFFAOYSA-N 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
239000000460 chlorine Chemical group 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
QAZGHRFRENNQAG-UHFFFAOYSA-N 4-[[3-[(3,4-dichlorophenyl)sulfonylamino]benzoyl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)C1=CC=CC(NS(=O)(=O)C=2C=C(Cl)C(Cl)=CC=2)=C1 QAZGHRFRENNQAG-UHFFFAOYSA-N 0.000 claims description 4
AGRUNZGNMCSMHG-UHFFFAOYSA-N 4-[[3-[(3,5-dichlorophenyl)sulfonylamino]-4,5-dimethoxybenzoyl]amino]benzoic acid Chemical compound COC=1C(OC)=CC(C(=O)NC=2C=CC(=CC=2)C(O)=O)=CC=1NS(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 AGRUNZGNMCSMHG-UHFFFAOYSA-N 0.000 claims description 4
JJLJGIRPFCBFKF-UHFFFAOYSA-N 4-[[3-[(3,5-dichlorophenyl)sulfonylamino]benzoyl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)C1=CC=CC(NS(=O)(=O)C=2C=C(Cl)C=C(Cl)C=2)=C1 JJLJGIRPFCBFKF-UHFFFAOYSA-N 0.000 claims description 4
ZAWAGPGGGPIRPE-UHFFFAOYSA-N 4-[[4-chloro-3-[(2,5-dichlorophenyl)sulfonylamino]benzoyl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)C1=CC=C(Cl)C(NS(=O)(=O)C=2C(=CC=C(Cl)C=2)Cl)=C1 ZAWAGPGGGPIRPE-UHFFFAOYSA-N 0.000 claims description 4
125000000842 isoxazolyl group Chemical group 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
125000003226 pyrazolyl group Chemical group 0.000 claims description 4
125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
125000001544 thienyl group Chemical group 0.000 claims description 4
BHCWEBPKGLAHJK-UHFFFAOYSA-N 3-[(3-chlorophenyl)sulfonylamino]-2-[4-(2h-tetrazol-5-yl)phenyl]benzamide Chemical compound C=1C=C(C=2NN=NN=2)C=CC=1C=1C(C(=O)N)=CC=CC=1NS(=O)(=O)C1=CC=CC(Cl)=C1 BHCWEBPKGLAHJK-UHFFFAOYSA-N 0.000 claims description 3
PALCFWIMZLSUPB-UHFFFAOYSA-N 4-[[3-(benzenesulfonamido)-4-chlorobenzoyl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)C1=CC=C(Cl)C(NS(=O)(=O)C=2C=CC=CC=2)=C1 PALCFWIMZLSUPB-UHFFFAOYSA-N 0.000 claims description 3
SMFZBOXTWIRUAJ-UHFFFAOYSA-N 4-[[3-[(5-chloro-2-methoxyphenyl)sulfonylamino]benzoyl]amino]benzoic acid Chemical compound COC1=CC=C(Cl)C=C1S(=O)(=O)NC1=CC=CC(C(=O)NC=2C=CC(=CC=2)C(O)=O)=C1 SMFZBOXTWIRUAJ-UHFFFAOYSA-N 0.000 claims description 3
ZXVNWQMGSFGEBN-UHFFFAOYSA-N 4-[[4-chloro-3-[(3,5-dichlorophenyl)sulfonylamino]benzoyl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)C1=CC=C(Cl)C(NS(=O)(=O)C=2C=C(Cl)C=C(Cl)C=2)=C1 ZXVNWQMGSFGEBN-UHFFFAOYSA-N 0.000 claims description 3
QRMUXWJBLWTWGW-UHFFFAOYSA-N 4-[[4-chloro-3-[(3-fluorophenyl)sulfonylamino]benzoyl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)C1=CC=C(Cl)C(NS(=O)(=O)C=2C=C(F)C=CC=2)=C1 QRMUXWJBLWTWGW-UHFFFAOYSA-N 0.000 claims description 3
OZMYHRRHEHWPLK-UHFFFAOYSA-N 4-[[4-chloro-3-[(5-chloro-2-methoxyphenyl)sulfonylamino]benzoyl]amino]benzoic acid Chemical compound COC1=CC=C(Cl)C=C1S(=O)(=O)NC1=CC(C(=O)NC=2C=CC(=CC=2)C(O)=O)=CC=C1Cl OZMYHRRHEHWPLK-UHFFFAOYSA-N 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
WSTRURFKGFXRKH-UHFFFAOYSA-N 4-[[3,4-dimethoxy-5-[[3-(trifluoromethyl)phenyl]sulfonylamino]benzoyl]amino]benzoic acid Chemical compound COC=1C(OC)=CC(C(=O)NC=2C=CC(=CC=2)C(O)=O)=CC=1NS(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 WSTRURFKGFXRKH-UHFFFAOYSA-N 0.000 claims description 2
MRSJEPWAAWETSO-UHFFFAOYSA-N 4-[[3-(benzenesulfonamido)-4,5-dimethoxybenzoyl]amino]benzoic acid Chemical compound COC=1C(OC)=CC(C(=O)NC=2C=CC(=CC=2)C(O)=O)=CC=1NS(=O)(=O)C1=CC=CC=C1 MRSJEPWAAWETSO-UHFFFAOYSA-N 0.000 claims description 2
VAMOJBUIMQCZJH-UHFFFAOYSA-N 4-[[3-[(2,5-dichlorophenyl)sulfonylamino]-4,5-dimethoxybenzoyl]amino]benzoic acid Chemical compound COC=1C(OC)=CC(C(=O)NC=2C=CC(=CC=2)C(O)=O)=CC=1NS(=O)(=O)C1=CC(Cl)=CC=C1Cl VAMOJBUIMQCZJH-UHFFFAOYSA-N 0.000 claims description 2
KWFXPHFQXSUTSU-UHFFFAOYSA-N 4-[[3-[(3,4-dichlorophenyl)sulfonylamino]-4,5-dimethoxybenzoyl]amino]benzoic acid Chemical compound COC=1C(OC)=CC(C(=O)NC=2C=CC(=CC=2)C(O)=O)=CC=1NS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 KWFXPHFQXSUTSU-UHFFFAOYSA-N 0.000 claims description 2
LUTMAEKOOIPNEN-UHFFFAOYSA-N 4-[[3-[(3-chlorophenyl)sulfonylamino]benzoyl]amino]-2-fluorobenzoic acid Chemical compound C1=C(F)C(C(=O)O)=CC=C1NC(=O)C1=CC=CC(NS(=O)(=O)C=2C=C(Cl)C=CC=2)=C1 LUTMAEKOOIPNEN-UHFFFAOYSA-N 0.000 claims description 2
JJFRXGVSICGPNT-UHFFFAOYSA-N 4-[[3-[(3-chlorophenyl)sulfonylamino]benzoyl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)C1=CC=CC(NS(=O)(=O)C=2C=C(Cl)C=CC=2)=C1 JJFRXGVSICGPNT-UHFFFAOYSA-N 0.000 claims description 2
NKIKHCUJVOSOKQ-UHFFFAOYSA-N 4-[[4-chloro-3-[(2,5-dimethoxyphenyl)sulfonylamino]benzoyl]amino]benzoic acid Chemical compound COC1=CC=C(OC)C(S(=O)(=O)NC=2C(=CC=C(C=2)C(=O)NC=2C=CC(=CC=2)C(O)=O)Cl)=C1 NKIKHCUJVOSOKQ-UHFFFAOYSA-N 0.000 claims description 2
BSLITOFRZHJCPW-UHFFFAOYSA-N 4-[[4-chloro-3-[(3-chlorophenyl)sulfonylamino]benzoyl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)C1=CC=C(Cl)C(NS(=O)(=O)C=2C=C(Cl)C=CC=2)=C1 BSLITOFRZHJCPW-UHFFFAOYSA-N 0.000 claims description 2
BKXTZPVSRKQZML-UHFFFAOYSA-N 5-[[3-[(3-chlorophenyl)sulfonylamino]benzoyl]amino]pyridine-2-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC=C1NC(=O)C1=CC=CC(NS(=O)(=O)C=2C=C(Cl)C=CC=2)=C1 BKXTZPVSRKQZML-UHFFFAOYSA-N 0.000 claims description 2
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125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 2
MUZKXPPYJNUSCX-UHFFFAOYSA-N 3-[(5-chloro-2-methoxyphenyl)sulfonylamino]-2-[4-(2h-tetrazol-5-yl)phenyl]benzamide Chemical compound COC1=CC=C(Cl)C=C1S(=O)(=O)NC1=CC=CC(C(N)=O)=C1C1=CC=C(C=2NN=NN=2)C=C1 MUZKXPPYJNUSCX-UHFFFAOYSA-N 0.000 claims 1
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SBBAGUKFWGACIS-UHFFFAOYSA-N ethyl 4-[[3,4-dimethoxy-5-[[3-(trifluoromethyl)phenyl]sulfonylamino]benzoyl]amino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)C1=CC(NS(=O)(=O)C=2C=C(C=CC=2)C(F)(F)F)=C(OC)C(OC)=C1 SBBAGUKFWGACIS-UHFFFAOYSA-N 0.000 description 1
CAHVWAWUBITVLE-UHFFFAOYSA-N ethyl 4-[[3-(benzenesulfonamido)-4,5-dimethoxybenzoyl]amino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)C1=CC(NS(=O)(=O)C=2C=CC=CC=2)=C(OC)C(OC)=C1 CAHVWAWUBITVLE-UHFFFAOYSA-N 0.000 description 1
HXXCYYHXHSXONJ-UHFFFAOYSA-N ethyl 4-[[3-(benzenesulfonamido)-4-chlorobenzoyl]amino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)C1=CC=C(Cl)C(NS(=O)(=O)C=2C=CC=CC=2)=C1 HXXCYYHXHSXONJ-UHFFFAOYSA-N 0.000 description 1
HRDKCZPZQUYUNA-UHFFFAOYSA-N ethyl 4-[[3-(benzenesulfonamido)benzoyl]amino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)C1=CC=CC(NS(=O)(=O)C=2C=CC=CC=2)=C1 HRDKCZPZQUYUNA-UHFFFAOYSA-N 0.000 description 1
HOEJDZCCNVSBSC-UHFFFAOYSA-N ethyl 4-[[3-(naphthalen-2-ylsulfonylamino)benzoyl]amino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)C1=CC=CC(NS(=O)(=O)C=2C=C3C=CC=CC3=CC=2)=C1 HOEJDZCCNVSBSC-UHFFFAOYSA-N 0.000 description 1
OCRJTNJUTIRGFS-UHFFFAOYSA-N ethyl 4-[[3-[(2,5-dichlorophenyl)sulfonylamino]-4,5-dimethoxybenzoyl]amino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)C1=CC(NS(=O)(=O)C=2C(=CC=C(Cl)C=2)Cl)=C(OC)C(OC)=C1 OCRJTNJUTIRGFS-UHFFFAOYSA-N 0.000 description 1
PYSMOHHPXUKHHL-UHFFFAOYSA-N ethyl 4-[[3-[(2-fluorophenyl)sulfonylamino]benzoyl]amino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)C1=CC=CC(NS(=O)(=O)C=2C(=CC=CC=2)F)=C1 PYSMOHHPXUKHHL-UHFFFAOYSA-N 0.000 description 1
KBAVBCDVMNSHPH-UHFFFAOYSA-N ethyl 4-[[3-[(2-methoxyphenyl)sulfonylamino]benzoyl]amino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)C1=CC=CC(NS(=O)(=O)C=2C(=CC=CC=2)OC)=C1 KBAVBCDVMNSHPH-UHFFFAOYSA-N 0.000 description 1
QAMHHBLPXIQOEE-UHFFFAOYSA-N ethyl 4-[[3-[(3,4-dichlorophenyl)sulfonylamino]benzoyl]amino]-2-methoxybenzoate Chemical compound C1=C(OC)C(C(=O)OCC)=CC=C1NC(=O)C1=CC=CC(NS(=O)(=O)C=2C=C(Cl)C(Cl)=CC=2)=C1 QAMHHBLPXIQOEE-UHFFFAOYSA-N 0.000 description 1
NNNPULOLUWTPOU-UHFFFAOYSA-N ethyl 4-[[3-[(3,4-dichlorophenyl)sulfonylamino]benzoyl]amino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)C1=CC=CC(NS(=O)(=O)C=2C=C(Cl)C(Cl)=CC=2)=C1 NNNPULOLUWTPOU-UHFFFAOYSA-N 0.000 description 1
HJDSNAHYTQOYFS-UHFFFAOYSA-N ethyl 4-[[3-[(3,5-dichlorophenyl)sulfonylamino]-4,5-dimethoxybenzoyl]amino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)C1=CC(NS(=O)(=O)C=2C=C(Cl)C=C(Cl)C=2)=C(OC)C(OC)=C1 HJDSNAHYTQOYFS-UHFFFAOYSA-N 0.000 description 1
RGCPRDUZDILVPX-UHFFFAOYSA-N ethyl 4-[[3-[(3,5-dichlorophenyl)sulfonylamino]benzoyl]amino]-2-methoxybenzoate Chemical compound C1=C(OC)C(C(=O)OCC)=CC=C1NC(=O)C1=CC=CC(NS(=O)(=O)C=2C=C(Cl)C=C(Cl)C=2)=C1 RGCPRDUZDILVPX-UHFFFAOYSA-N 0.000 description 1
FAYJTQNLBRHKAK-UHFFFAOYSA-N ethyl 4-[[3-[(3,5-dichlorophenyl)sulfonylamino]benzoyl]amino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)C1=CC=CC(NS(=O)(=O)C=2C=C(Cl)C=C(Cl)C=2)=C1 FAYJTQNLBRHKAK-UHFFFAOYSA-N 0.000 description 1
OVJACOPJYIQTPR-UHFFFAOYSA-N ethyl 4-[[3-[(3-chlorophenyl)sulfonylamino]-4,5-dimethoxybenzoyl]amino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)C1=CC(NS(=O)(=O)C=2C=C(Cl)C=CC=2)=C(OC)C(OC)=C1 OVJACOPJYIQTPR-UHFFFAOYSA-N 0.000 description 1
DPBASKVJPHPOMN-UHFFFAOYSA-N ethyl 4-[[3-[(3-chlorophenyl)sulfonylamino]benzoyl]amino]-2-methoxybenzoate Chemical compound C1=C(OC)C(C(=O)OCC)=CC=C1NC(=O)C1=CC=CC(NS(=O)(=O)C=2C=C(Cl)C=CC=2)=C1 DPBASKVJPHPOMN-UHFFFAOYSA-N 0.000 description 1
RZDOGXREIDUDFN-UHFFFAOYSA-N ethyl 4-[[3-[(3-chlorophenyl)sulfonylamino]benzoyl]amino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)C1=CC=CC(NS(=O)(=O)C=2C=C(Cl)C=CC=2)=C1 RZDOGXREIDUDFN-UHFFFAOYSA-N 0.000 description 1
ZFLWCSDIBLXTMY-UHFFFAOYSA-N ethyl 4-[[3-[(4-methoxyphenyl)sulfonylamino]benzoyl]amino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)C1=CC=CC(NS(=O)(=O)C=2C=CC(OC)=CC=2)=C1 ZFLWCSDIBLXTMY-UHFFFAOYSA-N 0.000 description 1
DOSCYIZNONJQTP-UHFFFAOYSA-N ethyl 4-[[3-[[5-(1,2-oxazol-3-yl)thiophen-2-yl]sulfonylamino]benzoyl]amino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)C1=CC=CC(NS(=O)(=O)C=2SC(=CC=2)C2=NOC=C2)=C1 DOSCYIZNONJQTP-UHFFFAOYSA-N 0.000 description 1
OLXGVNNIPVJWNE-UHFFFAOYSA-N ethyl 4-[[3-[[5-(2-methylsulfanylpyrimidin-4-yl)thiophen-2-yl]sulfonylamino]benzoyl]amino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)C1=CC=CC(NS(=O)(=O)C=2SC(=CC=2)C=2N=C(SC)N=CC=2)=C1 OLXGVNNIPVJWNE-UHFFFAOYSA-N 0.000 description 1
QTCLJOIXSSWYNH-UHFFFAOYSA-N ethyl 4-[[4-chloro-3-[(2,5-dimethoxyphenyl)sulfonylamino]benzoyl]amino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)C1=CC=C(Cl)C(NS(=O)(=O)C=2C(=CC=C(OC)C=2)OC)=C1 QTCLJOIXSSWYNH-UHFFFAOYSA-N 0.000 description 1
HSGYLQMCKQNKDU-UHFFFAOYSA-N ethyl 4-[[4-chloro-3-[(3,4-dichlorophenyl)sulfonylamino]benzoyl]amino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)C1=CC=C(Cl)C(NS(=O)(=O)C=2C=C(Cl)C(Cl)=CC=2)=C1 HSGYLQMCKQNKDU-UHFFFAOYSA-N 0.000 description 1
SCZVLHULSZAUOV-UHFFFAOYSA-N ethyl 4-[[4-chloro-3-[(3,5-dichlorophenyl)sulfonylamino]benzoyl]amino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)C1=CC=C(Cl)C(NS(=O)(=O)C=2C=C(Cl)C=C(Cl)C=2)=C1 SCZVLHULSZAUOV-UHFFFAOYSA-N 0.000 description 1
KVEGYXPUNAAYDG-UHFFFAOYSA-N ethyl 4-[[4-chloro-3-[(3-chlorophenyl)sulfonylamino]benzoyl]amino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)C1=CC=C(Cl)C(NS(=O)(=O)C=2C=C(Cl)C=CC=2)=C1 KVEGYXPUNAAYDG-UHFFFAOYSA-N 0.000 description 1
KOJOXHAGSSLQCE-UHFFFAOYSA-N ethyl 4-[[4-chloro-3-[(3-fluorophenyl)sulfonylamino]benzoyl]amino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)C1=CC=C(Cl)C(NS(=O)(=O)C=2C=C(F)C=CC=2)=C1 KOJOXHAGSSLQCE-UHFFFAOYSA-N 0.000 description 1
TVWORZRQIQGJCK-UHFFFAOYSA-N ethyl 4-[[4-chloro-3-[(5-chloro-2-methoxyphenyl)sulfonylamino]benzoyl]amino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)C1=CC=C(Cl)C(NS(=O)(=O)C=2C(=CC=C(Cl)C=2)OC)=C1 TVWORZRQIQGJCK-UHFFFAOYSA-N 0.000 description 1
ZTMVQCHSEGKJFV-UHFFFAOYSA-N ethyl 4-[[4-chloro-3-[[3-(trifluoromethoxy)phenyl]sulfonylamino]benzoyl]amino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)C1=CC=C(Cl)C(NS(=O)(=O)C=2C=C(OC(F)(F)F)C=CC=2)=C1 ZTMVQCHSEGKJFV-UHFFFAOYSA-N 0.000 description 1
LDVQRDYSANBBAL-UHFFFAOYSA-N ethyl 4-[[4-chloro-3-[[3-(trifluoromethyl)phenyl]sulfonylamino]benzoyl]amino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)C1=CC=C(Cl)C(NS(=O)(=O)C=2C=C(C=CC=2)C(F)(F)F)=C1 LDVQRDYSANBBAL-UHFFFAOYSA-N 0.000 description 1
CYXBQXFRXCNWCF-UHFFFAOYSA-N ethyl 4-amino-2-methoxybenzoate Chemical compound CCOC(=O)C1=CC=C(N)C=C1OC CYXBQXFRXCNWCF-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
HJUFTIJOISQSKQ-UHFFFAOYSA-N fenoxycarb Chemical compound C1=CC(OCCNC(=O)OCC)=CC=C1OC1=CC=CC=C1 HJUFTIJOISQSKQ-UHFFFAOYSA-N 0.000 description 1
239000007941 film coated tablet Substances 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
239000005454 flavour additive Substances 0.000 description 1
MHMNJMPURVTYEJ-UHFFFAOYSA-N fluorescein-5-isothiocyanate Chemical compound O1C(=O)C2=CC(N=C=S)=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 MHMNJMPURVTYEJ-UHFFFAOYSA-N 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
238000007710 freezing Methods 0.000 description 1
230000008014 freezing Effects 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000011521 glass Substances 0.000 description 1
229940028332 halog Drugs 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
239000003978 infusion fluid Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
229960004903 invert sugar Drugs 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000001786 isothiazolyl group Chemical group 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
230000000873 masking effect Effects 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000010534 mechanism of action Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
YRDPEKZBFANDFE-UHFFFAOYSA-N n-(3',6'-dihydroxy-1-oxospiro[2-benzofuran-3,9'-xanthene]-5-yl)-2-iodoacetamide Chemical compound O1C(=O)C2=CC=C(NC(=O)CI)C=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 YRDPEKZBFANDFE-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
OPECTNGATDYLSS-UHFFFAOYSA-N naphthalene-2-sulfonyl chloride Chemical compound C1=CC=CC2=CC(S(=O)(=O)Cl)=CC=C21 OPECTNGATDYLSS-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
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150000002828 nitro derivatives Chemical class 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000012038 nucleophile Substances 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000002674 ointment Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
125000001715 oxadiazolyl group Chemical group 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
BSCHIACBONPEOB-UHFFFAOYSA-N oxolane;hydrate Chemical compound O.C1CCOC1 BSCHIACBONPEOB-UHFFFAOYSA-N 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
235000019319 peptone Nutrition 0.000 description 1
CWCMIVBLVUHDHK-ZSNHEYEWSA-N phleomycin D1 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC[C@@H](N=1)C=1SC=C(N=1)C(=O)NCCCCNC(N)=N)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C CWCMIVBLVUHDHK-ZSNHEYEWSA-N 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
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239000000047 product Substances 0.000 description 1
QAQREVBBADEHPA-IEXPHMLFSA-N propionyl-CoA Chemical class O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CC)O[C@H]1N1C2=NC=NC(N)=C2N=C1 QAQREVBBADEHPA-IEXPHMLFSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
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238000012216 screening Methods 0.000 description 1
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239000002002 slurry Substances 0.000 description 1
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238000006467 substitution reaction Methods 0.000 description 1
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239000011975 tartaric acid Substances 0.000 description 1
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125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000012360 testing method Methods 0.000 description 1
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PCTNAMGLSYHIPL-UHFFFAOYSA-N tin(4+) tetraazide Chemical compound [Sn+4].[N-]=[N+]=[N-].[N-]=[N+]=[N-].[N-]=[N+]=[N-].[N-]=[N+]=[N-] PCTNAMGLSYHIPL-UHFFFAOYSA-N 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/18—Sulfonamides
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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- C07—ORGANIC CHEMISTRY
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- C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
- C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
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- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
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- C07—ORGANIC CHEMISTRY
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

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IL187409A 2005-06-06 2007-11-15 Sulfonamide derivatives useful as liver carnitine palmitoyl transferase (l-cpt1) inhibitors IL187409A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP05104904		2005-06-06
PCT/EP2006/062652 WO2006131452A1 (en)	2005-06-06	2006-05-29	SULFONAMIDE DERIVATIVES USEFUL AS LIVER CARNITINE PALMITOYL TRANSFERASE (L-CPTl) INHIBITORS

Publications (2)

Publication Number	Publication Date
IL187409A0 IL187409A0 (en)	2008-02-09
IL187409A true IL187409A (en)	2012-03-29

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ID=36940686

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL187409A IL187409A (en)	2005-06-06	2007-11-15	Sulfonamide derivatives useful as liver carnitine palmitoyl transferase (l-cpt1) inhibitors

Country Status (14)

Country	Link
US (4)	US7723538B2 (de)
EP (1)	EP1891001B1 (de)
JP (1)	JP4880678B2 (de)
KR (1)	KR100956703B1 (de)
CN (1)	CN101189210B (de)
AT (1)	ATE466838T1 (de)
AU (1)	AU2006256825B2 (de)
BR (1)	BRPI0610877A2 (de)
CA (1)	CA2608837C (de)
DE (1)	DE602006014139D1 (de)
ES (1)	ES2342842T3 (de)
IL (1)	IL187409A (de)
MX (1)	MX2007014927A (de)
WO (1)	WO2006131452A1 (de)

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MX295245B (es)	2005-06-21	2012-01-26	Mitsui Chemicals Inc	Derivado de amida e insecticida que contiene el mismo.
KR20080093123A (ko)	2006-02-13	2008-10-20	에프. 호프만-라 로슈 아게	당뇨병 치료용 헤테로바이사이클릭 설폰아마이드 유도체
US7799933B2 (en) *	2006-12-21	2010-09-21	Hoffman-La Roche Inc.	Sulfonamide derivatives
KR100847448B1 (ko) *	2007-03-22	2008-07-21	한국화학연구원	3-아릴-5-알킬-1,2,4-옥사다이아졸 유도체, 그 제조방법 및이를 포함하는 비만 예방 또는 치료용 조성물
ATE518857T1 (de) *	2007-06-01	2011-08-15	Hoffmann La Roche	Piperidin-amidderivate
WO2009002433A1 (en) *	2007-06-22	2008-12-31	Dara Biosciences, Inc.	Compositions and methods for treating skin disorders
JP2011525530A (ja) *	2008-06-24	2011-09-22	ダラ・バイオサイエンシズ，インコーポレイテッド	酵素阻害剤およびその使用
PE20130601A1 (es) *	2010-08-03	2013-05-30	Chiesi Farma Spa	Formulacion de polvo seco que comprende un inhidor de fosfodiesterasa
RU2578975C2 (ru) *	2010-08-03	2016-03-27	КЬЕЗИ ФАРМАЧЕУТИЧИ С.п.А.	Фармацевтический препарат, содержащий ингибитор фосфодиэстеразы
JP6347451B2 (ja) *	2013-08-02	2018-06-27	国立大学法人富山大学	（ベンゼンスルホニルアミノ）ベンズアミド誘導体およびそれらを有効成分とするｓｈｉｐ２阻害剤
CN104815154A (zh) *	2015-05-06	2015-08-05	山东宏济堂制药集团有限公司	一种清热润喉糖及其制备方法和应用
WO2021226076A1 (en) *	2020-05-04	2021-11-11	The Research Foundation For The State University Of New York	Positron imaging tomography imaging agent composition and method for detection of bacterial infection
KR102606541B1 (ko) *	2021-04-23	2023-11-29	가천대학교 산학협력단	바이페닐설폰아마이드 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 글루카곤 수용체 활성 관련 질환의 예방 또는 치료용 약학적 조성물

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WO1998000134A1 (en) *	1996-06-28	1998-01-08	Merck & Co., Inc.	Fibrinogen receptor antagonists
AU709631B2 (en) *	1996-06-28	1999-09-02	Merck & Co., Inc.	Fibrinogen receptor antagonist prodrugs
JP2001526255A (ja) *	1997-12-23	2001-12-18	ワーナー−ランバート・カンパニー	炎症性疾患およびアテローム性動脈硬化症を治療または予防するチオ尿素およびベンズアミド化合物、組成物並びに方法
IT1299266B1 (it) *	1998-05-15	2000-02-29	Sigma Tau Ind Farmaceuti	Inibitori reversibili della carnitina palmitoil trasferasi
JP2001031652A (ja) *	1998-06-19	2001-02-06	Nissan Chem Ind Ltd	六員環複素環類
JP2004155788A (ja) *	1998-09-24	2004-06-03	Tanabe Seiyaku Co Ltd	腎疾患治療薬およびそのスクリーニング方法
CA2474884A1 (en) *	2002-02-08	2003-08-14	John Hopkins University School Of Medicine	Stimulation of cpt-1 as a means to reduce weight
US20050113450A1 (en) *	2002-08-23	2005-05-26	Atli Thorarensen	Antibacterial agents
US20090105218A1 (en) *	2004-05-29	2009-04-23	7Tm Pharma A/S	CRTH2 Receptor Ligands For Therapeutic Use

2006
- 2006-05-29 BR BRPI0610877-6A patent/BRPI0610877A2/pt not_active IP Right Cessation
- 2006-05-29 AT AT06763311T patent/ATE466838T1/de active
- 2006-05-29 WO PCT/EP2006/062652 patent/WO2006131452A1/en not_active Ceased
- 2006-05-29 JP JP2008515181A patent/JP4880678B2/ja not_active Expired - Fee Related
- 2006-05-29 CA CA2608837A patent/CA2608837C/en not_active Expired - Fee Related
- 2006-05-29 KR KR1020077028409A patent/KR100956703B1/ko not_active Expired - Fee Related
- 2006-05-29 AU AU2006256825A patent/AU2006256825B2/en not_active Ceased
- 2006-05-29 EP EP06763311A patent/EP1891001B1/de not_active Not-in-force
- 2006-05-29 MX MX2007014927A patent/MX2007014927A/es active IP Right Grant
- 2006-05-29 CN CN200680019219XA patent/CN101189210B/zh not_active Expired - Fee Related
- 2006-05-29 DE DE602006014139T patent/DE602006014139D1/de active Active
- 2006-05-29 ES ES06763311T patent/ES2342842T3/es active Active
- 2006-06-01 US US11/444,765 patent/US7723538B2/en not_active Expired - Fee Related
2007
- 2007-11-15 IL IL187409A patent/IL187409A/en not_active IP Right Cessation
2010
- 2010-02-08 US US12/701,769 patent/US20100144762A1/en not_active Abandoned
2011
- 2011-09-07 US US13/226,697 patent/US20110319438A1/en not_active Abandoned
2012
- 2012-05-22 US US13/477,336 patent/US20120232104A1/en not_active Abandoned

Also Published As

Publication number	Publication date
AU2006256825B2 (en)	2010-02-18
US20120232104A1 (en)	2012-09-13
ATE466838T1 (de)	2010-05-15
AU2006256825A1 (en)	2006-12-14
US20100144762A1 (en)	2010-06-10
KR20080008401A (ko)	2008-01-23
CN101189210B (zh)	2012-06-06
ES2342842T3 (es)	2010-07-15
WO2006131452A1 (en)	2006-12-14
CA2608837C (en)	2011-08-02
US20060276494A1 (en)	2006-12-07
EP1891001B1 (de)	2010-05-05
BRPI0610877A2 (pt)	2010-08-03
CA2608837A1 (en)	2006-12-14
IL187409A0 (en)	2008-02-09
EP1891001A1 (de)	2008-02-27
JP2008545770A (ja)	2008-12-18
US20110319438A1 (en)	2011-12-29
KR100956703B1 (ko)	2010-05-06
MX2007014927A (es)	2008-02-15
DE602006014139D1 (de)	2010-06-17
US7723538B2 (en)	2010-05-25
JP4880678B2 (ja)	2012-02-22
CN101189210A (zh)	2008-05-28

Legal Events

Date	Code	Title
2012-07-31	FF	Patent granted
2012-07-31	KB	Patent renewed
2016-12-29	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
IL187409A (en)	2012-03-29	Sulfonamide derivatives useful as liver carnitine palmitoyl transferase (l-cpt1) inhibitors
US7858645B2 (en)	2010-12-28	Indazole derivatives
US7799933B2 (en)	2010-09-21	Sulfonamide derivatives
EP2188266B1 (de)	2012-10-17	Neuartige Piperazinamid-Derivate
KR101089878B1 (ko)	2011-12-05	간 카르니틴 팔미토일 트랜스퍼라제의 억제제로서 유용한신규 헤테로바이사이클릭 유도체
WO2009150109A1 (en)	2009-12-17	Imidazolidine derivatives
CA2787914C (en)	2018-10-09	Therapeutic agents for treatment of ocular hypertension
CA2622334C (en)	2011-03-22	Thiophene derivatives for the treatment of diabetes